Tropatepine

Tropatepine
Clinical data
Trade names	Lepticur
AHFS/Drugs.com	International Drug Names
ATC code	N04AA12 (WHO) ;
Identifiers
	IUPAC name (1S,5S)-3-dibenzo[b,e]thiepin-11(6H)-ylidene-8-methyl-8-azabicyclo[3.2.1]octane;
CAS Number	27574-24-9;
PubChem CID	198068;
ChemSpider	171431 ;
UNII	C27HY5RFU5;
KEGG	D07303 ;
CompTox Dashboard (EPA)	DTXSID70865380 ;
Chemical and physical data
Formula	C22H23NS
Molar mass	333.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES S3c1ccccc1/C(c2c(cccc2)C3)=C5/CC4N(C)C(CC4)C5;
	InChI InChI=1S/C22H23NS/c1-23-17-10-11-18(23)13-16(12-17)22-19-7-3-2-6-15(19)14-24-21-9-5-4-8-20(21)22/h2-9,17-18H,10-14H2,1H3 ; Key:JOQKFRLFXDPXHX-UHFFFAOYSA-N ;
	(verify)

Tropatepine (brand name Lepticur) is an anticholinergic used as an antiparkinsonian agent.^[1]

Synthesis

Tropatepine can be synthesized from 3-chlorotropane (1).^[2] A Grignard reaction between 3-chlorotropane and dibenzo[b,e]thiepin-11(6H)-one (2) followed by dehydration to the olefin produces tropatepine (3).

Synthesis of tropatepine

References

^ Celsis P, Montastruc JL, Rascol O, Senard JM, Marc-Vergnes JP, Rascol A (July 1989). "Effect of tropatepine, an anticholinergic drug, on regional cerebral blood flow in patients with Parkinson's disease". Journal of Neurology, Neurosurgery, and Psychiatry. 52 (7): 917–8. doi:10.1136/jnnp.52.7.917. PMC 1031949. PMID 2769291.
^ DE1952206 idem J Boissier, R Ratouis, U.S. patent 3,725,415 (1973 to Ind Pour La Fab Antibiotiques).

[1] Celsis P, Montastruc JL, Rascol O, Senard JM, Marc-Vergnes JP, Rascol A (July 1989). "Effect of tropatepine, an anticholinergic drug, on regional cerebral blood flow in patients with Parkinson's disease". Journal of Neurology, Neurosurgery, and Psychiatry. 52 (7): 917–8. doi:10.1136/jnnp.52.7.917. PMC 1031949. PMID 2769291.

[2] DE1952206 idem J Boissier, R Ratouis, U.S. patent 3,725,415 (1973 to Ind Pour La Fab Antibiotiques).

[1]

[2]

Tropatepine

Synthesis

See also

References